Method for synthesizing AE-active ester

A synthesis method and technology of active ester, applied in the direction of organic chemistry, etc., can solve the problems of unstable structure of AE-active ester, short storage time, storage and use restriction, etc., to achieve great implementation value and economic benefits, easier storage, lower The effect of production costs

Active Publication Date: 2010-06-23
YIYUAN XINQUAN CHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] However, the structure of the generated AE-active ester is unstable and the sto

Method used

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  • Method for synthesizing AE-active ester

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Experimental program
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Effect test

Embodiment 1

[0019] The molar ratio of the feedstocks is hydrothiazide: dithiodibenzothiazole: triethylamine: triethyl phosphite=1:1.2:1:2.5. The volume ratio of mixed solvent: dichloromethane and acetonitrile is 1.5:1. Axamic acid: glyceryl tristearate: mixed solvent = 20g: 0.6g: 150ml.

[0020] Add 20g of aminothiaxamic acid to a 500mL three-necked flask equipped with mechanical stirring, constant pressure dropping funnel and thermometer, add dithiodibenzothiazole and mixed solvent in proportion, stir well, add glyceryl tristearate, and stir at room temperature Add triethylamine and triethyl phosphite, control the temperature at 25°C to react for 3h, cool to 5°C in an ice bath, filter, wash the filter cake with methanol at 5°C, and dry under vacuum to obtain 26.33g of AE-active ester. The yield was 89%, the content was 99.1% (HPLC), and the purity was 99.57%.

Embodiment 2

[0022] The molar ratio of the feedstock is hydrothiasic acid: dithiodibenzothiazole: triethylamine: triethyl phosphite=1:1.2:1:2.5. The volume ratio of mixed solvent: dichloromethane and acetonitrile is 1.2:1. Axamic acid: glyceryl tristearate: mixed solvent = 20g: 1.6g: 150ml.

[0023] Add 20g of aminothiaxamic acid to a 500mL three-necked flask equipped with mechanical stirring, constant pressure dropping funnel and thermometer, add dithiodibenzothiazole and mixed solvent in proportion, stir well, add glyceryl tristearate, and stir at room temperature Add triethylamine and triethyl phosphite, control the temperature at 25°C to react for 3h, cool to 5°C in an ice bath, filter, wash the filter cake with methanol at 5°C, and dry in vacuum to obtain 27.51g of AE-active ester. The yield was 93%, the purity was 99.3% (HPLC), and the content was 99.8%.

Embodiment 3

[0025] The molar ratio of the feedstock is hydrothiasic acid: dithiodibenzothiazole: triethylamine: triethyl phosphite=1:1.2:1:2.5. The volume ratio of mixed solvent: dichloromethane and acetonitrile is 1.6:1. Axamic acid: glyceryl tristearate: mixed solvent = 20g: 1.2g: 200ml.

[0026] Add 20g of aminothiaxamic acid to a 500mL three-necked flask equipped with mechanical stirring, constant pressure dropping funnel and thermometer, add glyceryl tristearate and mixed solvent in proportion, stir evenly, add dithiodibenzothiazole, stir at room temperature Add triethylamine phosphite, then add triethyl, control the temperature at 25°C to react for 3h, cool to 5°C in an ice bath, filter, wash the filter cake with methanol at 5°C, and dry under vacuum to obtain 26.92g of AE-active ester. The yield was 91%, the content was 99.0% (HPLC), and the purity was 99.62%.

[0027] Compared with the traditional synthesis method, the invention has the advantages of cheap and readily available raw m...

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Abstract

The invention discloses a method for synthesizing AE-active ester. The AE-active ester is prepared by taking aminothiazoly loximate and dithio-bisbenzothiazole as raw materials and carrying out condensation reaction in the presence of triethylamine and triethyl-phosphite. The method is characterized in that higher fatty acid with diffusion effect is introduced into the condensation reaction and a mixed solvent consisting of methylene dichloride and acetonitrile is adopted, wherein the volume ratio of the methylene dichloride to the acetonitrile is (1.2-1.6):1. On the basis of the traditional process, the invention introduces a dispersion agent with diffusion effect, overcomes the defects of unstable structure and short preservation time of the AE-active ester, ensures that products are easy to preserve, changes a reaction solvent system and improves the yield up to over 91 percent. In addition, the solvent can be recycled so as to reduce the production cost and has higher implementation benefit and economic benefit.

Description

Technical field [0001] The invention relates to a method for synthesizing AE-active ester. By adding a dispersant with diffusion effect, the structure of AE-active ester is more stable and the storage time is longer. Background technique [0002] AE-active ester, chemical name: 2-methoxyimino-2-(2-amino-4-thiazolyl)-(z)-thioacetic acid benzothiazole ester. Appearance: white or light yellow crystalline powder, melting point: 128~130℃. Low toxicity and bitter taste, easily soluble in acetone and tetrahydrofuran, slightly soluble in acetonitrile and dichloromethane, insoluble in water, and can burn when exposed to an open flame. [0003] AE-active ester is one of the important side chains of semi-synthetic cephalosporin antibiotics. It is the third and fourth generation semi-synthetic cephalosporins such as synthetic cefotaxime sodium, ceftriaxone sodium, cefpiime, and cefpirome An indispensable intermediate. [0004] The traditional production process is prepared by condensation rea...

Claims

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Application Information

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IPC IPC(8): C07D277/40
Inventor 周磊蔡杰陈国伟许京兰杨萍萍
Owner YIYUAN XINQUAN CHEM
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